MXPA06009070A - Fungicidal composition comprising a pyridylethylbenzamide derivative and a compound capable of inhibiting the transport of electrons of the respiratory chain in phytopathogenic fungal organisms - Google Patents
Fungicidal composition comprising a pyridylethylbenzamide derivative and a compound capable of inhibiting the transport of electrons of the respiratory chain in phytopathogenic fungal organismsInfo
- Publication number
- MXPA06009070A MXPA06009070A MXPA/A/2006/009070A MXPA06009070A MXPA06009070A MX PA06009070 A MXPA06009070 A MX PA06009070A MX PA06009070 A MXPA06009070 A MX PA06009070A MX PA06009070 A MXPA06009070 A MX PA06009070A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- composition according
- inhibiting
- compound capable
- fungal organisms
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 157
- 239000000203 mixture Substances 0.000 title claims abstract description 127
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 37
- 230000003032 phytopathogenic Effects 0.000 title claims abstract description 28
- 230000002538 fungal Effects 0.000 title claims abstract description 26
- 230000000855 fungicidal Effects 0.000 title claims abstract description 18
- 230000035806 respiratory chain Effects 0.000 title claims abstract description 16
- 241000233866 Fungi Species 0.000 claims abstract description 12
- -1 amino, phenoxy Chemical group 0.000 claims description 38
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- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective Effects 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- 238000004642 transportation engineering Methods 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 239000004560 ultra-low volume (ULV) liquid Substances 0.000 description 1
- 239000004555 ultra-low volume (ULV) suspension Substances 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000004553 water soluble powder for seed treatment Substances 0.000 description 1
- 239000004554 water soluble tablet Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Abstract
A composition comprising at least a pyridylethylbenzamide derivative of general formula (I) (a) and a compound capable of inhibiting the transport of electrons of the respiratory chain in phytopathogenic fungal organisms (b) in a (a) / (b) weight ratio of from 0.01 to 20. A composition further comprising an additional fungicidal compound. A method for preventively or curatively combating the phytopathogenic fungi of crops by using this composition.
Description
FUNGICIDE COMPOSITION COMPRISING A PYRIDILETILBENZAMIDE DERIVATIVE AND A COMPOUND CAPABLE OF INHIBITING THE
TRANSPORTATION D? ELECTRONS D? THE RESPIRATORY CHAIN IN
PHYTOPATHOGENIC FUNGAL ORGANISMS
FIELD OF THE INVENTION The present invention relates to novel fungicidal compositions comprising a pyridylethylbenzamide derivative and a compound capable of inhibiting electron transport of the respiratory chain in phytopathogenic fungal organisms. The present invention also relates to a method for combating or controlling phytopathogenic fungi by application to an infected or susceptible site of such composition. BACKGROUND OF THE INVENTION In the international patent application WO 01 / 11,965, numerous pyridylethylbenzamide derivatives are generically described. The possibility of combining one or more of these numerous pyridylethylbenzamide derivatives with known fungicidal products to develop a fungicidal activity is described in general terms, without a specific example or biological data. It is always of great interest in agriculture to use novel pesticidal mixtures that show a synergistic effect to avoid or to control notably the development of strains REF: i73871 resistant to the active ingredients or to the mixtures of known active ingredients used by the farmer while minimizing the dose of chemical products spread in the environment and reduce the cost of treatment. Now we have found some novel fungicidal compositions that possess the characteristics mentioned above. DETAILED DESCRIPTION OF THE INVENTION Accordingly, the present invention relates to a composition comprising: a) a pyridylethylbenzamide derivative of the general formula
in which: - p is an integer equal to l, 2, 3 or; - q is an integer equal to 1, 2, 3, 4 or 5; - each substituent X is chosen, independently of the others, as being: halogen, alkenyl or haloalkyl; - each substituent Y is chosen, independently of the others, as being: halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, amino, phenoxy, alkylthio, dialkylamino, acyl, cyano, ester, hydroxy, aminoalkyl, benzyl, haloalkoxy, halosulfonyl, halothioalkyl, alkoxyalkenyl, alkylsulfonamide, nitro, alkylsulfonyl, phenylsulfonyl or benzylsulfonyl; as to the N-oxides of the compounds thereof; and b) a compound capable of inhibiting the transport of electrons from the respiratory chain in phytopathogenic fungal organisms; in a weight ratio (a) / (b) from 0.01 to 20. In the context of the present invention, a compound capable of inhibiting electron transport of the respiratory chain in phytopathogenic fungal organisms is selected from the group comprising : a compound capable of inhibiting reduced nicotinamide adenine dinucleotide (NADH) dehydrogenase in phytopathogenic fungal organisms, a compound capable of inhibiting succinate dehydrogenase in phytopathogenic fungal organisms and a compound capable of inhibiting mitochondrial ubiquinol: ferricytochrome-c-oxidoreductase in phytopathogenic fungal organisms. A compound capable of inhibiting NADH dehydrogenase in phytopathogenic fungal organisms is also known as a complex I inhibitor. A compound capable of inhibiting electron transport of the respiratory chain of succinate dehydrogenase in phytopathogenic fungal organisms is also known as a complex II inhibitor.
A compound capable of inhibiting mitochondrial ubiquinol: ferricytochrome-c-oxidoreductase in phytopathogenic fungal organisms is also known as a complex III inhibitor. In the context of the present invention: halogen means: chlorine, bromine, iodine or fluorine; - each of the alkyl or acyl radicals present in the molecule contains from 1 to 10 carbon atoms, preferably. from 1 to 7 carbon atoms, more preferably from 1 to 5 carbon atoms and can be linear or branched; each of the alkenyl or alkynyl radicals present in the molecule contains from 2 to 10 carbon atoms, preferably from 2 to 7 carbon atoms, more preferably from 2 to 5 carbon atoms and can be linear or branched. The composition according to the present invention provides a synergistic effect. This synergistic effect allows a reduction of the chemical substances that are scattered in the environment and a reduction of the cost of the fungal treatment. In the context of the present invention, Coiby defines the terminology "synergistic effect" according to the article entitled "Calculation of the synergistic and antagonistic responses of herbicide combinations" Weeds, (1967), 15, pages 20-22. The last article mentions the formula: x * and E = x + y - loo "
wherein E represents the predicted percentage of inhibition of the disease by the combination of the two fungicides in defined doses (eg, equal ax and respectively), x is the percentage of inhibition observed for the disease by the compound (I) at a dose defined (equal to x) and is the percentage of inhibition observed for the disease by the compound (II) at a defined dose (equal to y). When the percentage of inhibition observed for the combination is greater than E, there is a synergistic effect. The composition according to the present invention comprises a pyridylethylbenzamide derivative of general formula (I). Preferably, the present invention relates to a composition comprising a pyridylethylbenzamide derivative of general formula (I) in which the different characteristics can be chosen singly or in combination as being: - as regards p, p is 2; as regards q, q is 1 or 2. More preferably, q is 2; as regards X, X is chosen, independently of the others, as being halogen or haloalkyl. More preferably, X is chosen, independently of the others, as being a chlorine atom or a trifluoromethyl group;
as regards Y, Y is chosen, independently of the others, as being halogen or haloalkyl. More preferably, Y is chosen, independently of the others, as being a chlorine atom OR a trifluoromethyl group; More preferably, the pyridylethylbenzamide derivative of the general formula (I) present in the composition of the present invention is: - N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2- trifluoromethylbenzamide (compound 1); -? -. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2- iodobenzamide (compound 2) or N-. { 2- [3,5-dichloro-2-pyridinyl] ethyl} -2- trifluoromethylbenzamide (compound 3). Even more preferably, the pyridylethylbenzamide derivative of the general formula (I) present in the composition of the present invention is N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoromethylbenzamide
(compound 1). The composition according to the present invention comprises a compound capable of inhibiting the transport of electrons from the respiratory chain. Preferably, the present invention also relates to a composition comprising a complex I inhibitor. More preferably, the present invention relates to a composition comprising a complex I inhibitor that is diflumetorin. Preferably, the present invention is also referred to to a composition comprising a complex II inhibitor More preferably, the present invention relates to a composition comprising a complex II inhibitor selected from the carboxamide derivatives which may be for example: N- [2- (1, 3-dimethyl-butyl) -phenyl] -5-fluoro-l, 3-dimethyl-lH-pyrazole-4-carboxamide, N- (3 ',' -dichloro-5-fluoro-biphenyl-2-yl) -3- ( difluoro-methyl) -l-methyl-lH-pyrazole-4-carboxamide, N- [2- (1, 3-dimethylbutyl) -thiophen-3-yl] -1-methyl-3- (trifluoromethyl) -lH-pyrazole- 4-carboxamide, benodanil, carboxy, fenfuram, flutolanil, furametpyr, mepronil, boscalid, oxycarboxine, trifluzamide N- [2- (1,3-dimethyl) is preferred l-butyl) -phenyl] -5-fluoro-l, 3-dimethyl-lH-pyrazole-4-carboxamide, N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -3- (difluoro -methyl) -l-methyl-lH-pyrazole-4-carboxamide, boscalid and oxycarboxin. Preferably, the present invention also relates to a composition comprising a complex III inhibitor. More preferably, the present invention relates to a composition comprising a complex III inhibitor selected from: strobilurin derivatives, ciazofamid, fenamidone or famoxadone. Fenamidone is preferred. Also preferred are strobilurin derivatives.
According to the present invention, the strobilurin derivatives can be, for example: azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifrioxystrobin, piradostrobin, picoxystrobin or 2-. { 2- [6- (3-Chloro-2-methylphenoxy) -5-fluoro-pyrimidin-4-yloxy] -phenyl} 2- methoxyimino-N-methylacetamide. 2- are preferred. { 2- [6- (3-Chloro-2-methylphenoxy) -5-fluoro-pyrimidin-4-yloxy] -phenyl} -2- methoxyimino- N-methylacetamide, azoxystrobin, trifloxystrobin and fluoxastrobin. The composition according to the present invention comprises: (a) at least one pyridylethylbenzamide derivative of general formula (I) and (b) a compound capable of inhibiting electron transport of the respiratory chain in phytopathogenic fungal organisms in a weight ratio (a) / (b) from 0.01 to 20; preferably from 0.05 to 10; even more preferably from 0.1 to 5. The composition of the present invention may further comprise at least one other fungicidal active ingredient different (c). The fungicidal active ingredient (c) can be selected from: azaconazole, azoxystrobin, (Z) -N- [a- (cyclopropylmethoxyimino) -2, 3-difluoro-6- (trifluoromethyl) benzyl] -2-phenylacetamide, 6-iodine -2-propoxy-3-propylquinazolin-4 (3H) -one, benalaxyl, benomyl, benthiavalicarb, biphenyl, bitertanol, blasticidin-S, boscalid, borax, bromuconazole, bupirimate, sec-butylamine, calcium polysulfide, captafol, captan, carbendazim, carboxy, carpropamid, quinometionat, chlorothalonil, clozolinate, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, cuprous oxide, cysoxamid, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, diclofluanide, dichlorophene, diclobutrazol, diclocymet , diclomezine, dicloran, _ dietofencarb, difenoconazole, diphenzoquat methylisulfate, difenzoquat, diflumetorim, dimethirimol, dimetomorph, diniconazole, dinobutone, dinocap, diphenylamine, dithianon, dodemorf, dodemorf acetate, dodine, edifenfos, epoxiconazole, etaboxam, ethaconazole, eti rimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenpiclonil, fenoxanil, fenpropidin, phenpropimorf, fentin, fentin hydroxide, fentin acetate, ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, formaldehyde, fosetyl, fosetyl-aluminum, fuberidazole, furalaxyl, furametpyr, guazatine, acetates of guazatine, hexachlorobenzene, hexaconazole, 8-hydroxyquinoline sulfate, potassium hydroxyquinolinesulfate, himexazole, imazalil sulfate, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iproben, iprodione, iprovalicarb, isoprothiolane, kasugamycin, hydrated kasugamycin hydrochloride, kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, mercuric chloride, mercuric oxide, mercuric chloride , metalaxyl, metalaxyl-M, metam-sodium, metam, metconazole, metasulfocarb, isothiocyanate lime, metiram, methominostrobin, mildiomycin, myclobutanil, nabam, nickel bis (dimethyldithiocarbamate), nitrotal-isopropyl, nuarimol, octylinone, ofurace, oleic acid, oxadixyl, oxina-copper, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencicuron, pentachlorophenol, sodium pentachlorophenoxide, pentachlorophenyl laurate, phenylmercury acetate, sodium 2-phenylphenoxide, 2-phenylphenol, phosphorous acid, phthalide, picoxystrobin, piperalin, polyoxinspolioxin B, polyoxin, polyoxorim, probenazole, prochloraz, procyamidone, propamocarb hydrochloride, propamocarb, propiconazole, propineb, protioconazole, pyraclostrobin, pyrazophos, pyributicarb, pyrifenox, pyrimethanil, pyroquilon, quinoxifen, quintozene, silthiopham, simeconazole, spiroxane, sulfur, tar oils, tebuconazole, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl , strip, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, triciclazole, tridemorph, trifloxis trolley, triflumizole, triforine, triticonazole, validamycin, vinclozolin, zineb, ziram and zoxamide. Preferably, the fungicidal active ingredient (c) is selected from: captan, folpet, dodine, propineb, mancozeb, thiram, tolylfluanid, iminoctadine, dithianon, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, fosetyl-Al , phosphorous acid, cymoxanil, iprovalicarb, bentiavalicarb, chlorothalonil, propamocarb, protioconazole, tebuconazole and spiroxamine. When the third active ingredient (c) as defined above is present in the composition, this compound may be present in a weight ratio amount (a): (b): (c) of 1: 0.01: 0 , 01 to 1: 20: 20 varying the ratios of compound (a) and compound (c) independently of one another. Preferably, the weight ratio (a): (b): (c) can be 1: 0, 05: 0.05 to 1: 10: 10. The following compositions may be cited to illustrate in an unrestricted manner the present invention: compound 1 with diflumetorin, compound 1 with N- [2- (1, 3-dimethyl- butyl) -phenyl] -5-fluoro-1,3-dimethyl-lH-pyrazole-4-carboxamide, compound 1 with N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -3- ( difluoro-methyl) -l-methyl-lH-pyrazole-4-carboxamide, compound 1 with N- [2- (1,3-dimethylbutyl) -thiophen-3-yl] -1-methyl-3- (trifluoromethyl) -lH -pyrazol-4-carboxamide, compound 1 with benodanil, compound 1 with carboxin, compound 1 with fenfuram, compound 1 with flutolanil, compound 1 with furametpyr, compound 1 with mepronil, compound 1 with boscalid, compound 1 with oxycarboxin, compound 1 with tifluzamide, compound 1 with ciazofamid, compound 1 with fenamidone, compound 1 with famoxadone. Azoxystrobin, compound 1 with dimoxystrobin, compound 1 with fluoxastrobin, compound 1 with kresoxim-methyl, compound 1 with metominostrobin, compound 1 with trifloxystrobin, compound 1 with piradostrobin, compound 1 with picoxystrobin, compound 1 with 2-. { 2- [6- (3-Chloro-2-methylphenoxy) -5-fluoro-pyrimidin-4-yloxy] -phenyl} 2-methoxyimino-N-methylacetamide, compound 2 with diflumetorin, compound 2 with N- [2- (1, 3-dimethyl-butyl) -phenyl] -5-fluoro-l, 3-dimethyl-lH-pyrazole-4- carboxamide, compound 2 with N- (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -3- (difluoromethyl) -l-methyl-1H-pyrazole-4-carboxamide, compound 2 with N- [2- (1, 3-dimethylbutyl) -thiophen-3-yl] -1-methyl-3- (trifluoromethyl) -lH-pyrazole-4-carboxamide, compound 2 with benodanil, compound 2 with carboxy, compound 2 with fenfuram, compound 2 with flutolanil, compound 2 with furametpyr, compound 2 with mepronil, compound 2 with boscalid, compound 2 with oxycarboxin, compound 2 with tifluzamide, compound 2 with ciazofamid, compound 2 with phenamidone, compound 2 with famoxadone. Azoxystrobin, compound 2 with dimoxystrobin, compound 2 with fluoxastrobin, compound 2 with kresoxim-methyl, compound 2 with metominostrobin, compound 2 with trifloxystrobin, compound 2 with piradostrobin, compound 2 with picoxystrobin, compound 2 with 2 ~. { 2 ~ [6- (3-Chloro-2-ethylphenoxy) -5-fluoro-pyrimidin-4-yloxy] -phenyl} 2-methoxyimino-N-methylacetamide, compound 3 with diflumetorin, compound 3 with? - [2- (1,3-dimethyl-butyl) -phenyl] -5-fluoro-1,3-dimethyl-lH-pyrazole-4- carboxamide, compound 3 with N- (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -3- (difluoromethyl) -l-methyl-1H-pyrazole-4-carboxamide, compound 3 with N- [2- (1, 3-dimethylbutyl) -thiophen-3-yl] -1-methyl-3- (trifluoromethyl) -lH-pyrazole-4-carboxamide, compound 3 with benodanil, compound 3 with carboxin, compound 3 with fenfuram, compound 3 with flutolanil, compound 3 with furametpyr, compound 3 with mepronil, compound 3 with b? scalid, compound 3 with oxycarboxine, compound 3 with tifluzamide, compound 3 with cysophamid, compound 3 with phenamidone, compound 3 with famoxadone. Azoxystrobin, compound 3 with dimoxystrobin, compound 3 with fluoxastrobin, compound 3 with kresoxim-methyl, compound 3 with metominostrobin, compound 3 with trifloxystrobin, compound 3 with piradostrobin, compound 3 with picoxystrobin, compound 3 with 2-. { 2- [6- (3-Chloro-2-methylphenoxy) -5-fluoro-pyrimidin-4-yloxy] -phenyl} 2-methoxyimino-N-methylacetamide. The composition according to the present invention may further comprise another additional component as an agriculturally acceptable support, carrier or filler material.
In the present description, the term "support" refers to an organic or inorganic material, natural or synthetic, with which the active material is combined to make it more easily applicable, in particular to the parts of the plant. Thus, this support is generally inert and should be acceptable from the agricultural point of view. The support can be a solid or a liquid. Examples of suitable supports include: clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, water, alcohols, in particular butanol, organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such supports can also be used. The composition may also comprise other additional components. In particular, the composition may further comprise a surfactant. The surfactant can be an emulsifier, a dispersing agent or a wetting agent, of ionic or non-ionic type or a mixture of said surfactants. Mention may be made, for example, of poly (acrylic acid) salts, 1-enosulfonic acid salts, salts of phenolsulfonic or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (in in particular alkylphenols or arylphenols), salts of esters of sulfosuccinic acid, taurine derivatives (in particular alkyl taurates), phosphoric esters of polyoxyethylated alcohols or phenols, fatty acid esters of polyols and derivatives of the above compounds containing sulfate, sulfonate functions and phosphate. The presence of at least one surfactant is in general essential when the active material and / or the inert support is insoluble in water and when the vector agent for the application is water. Preferably, the surfactant content may be between 5% and 40% by weight of the composition. Additional components may also be included, for example, protective colloids, adhesives, thickeners, thixotropic agents, penetrating agents, stabilizers, sequestering agents. More generally, the active materials can be combined with any solid or liquid additive, which is adapted to conventional formulation techniques. In general, the composition according to the invention may contain from 0.05 to 99% (by weight) of active material, preferably 10 to 70% by weight. The compositions according to the present invention can be used in various forms such as: aerosol dispenser, capsule suspension, cold fog concentrate, powder, emulsifiable concentrate, oil in water emulsion, water in oil emulsion, encapsulated granule, fine granule, concentrate that can flow for seed treatment, gas (under pressure), gas generating product, granules, hot fog concentrate, macrogranules, microgranules, oil dispersible powder, concentrate that can flow miscible in oil, miscible liquid in oil, paste, vegetable rod, powder for dry treatment of seeds, seeds coated with a pesticide, soluble concentrate, soluble powder, solution for treatment of seeds, concentrate in suspension (concentrate that can flow), ultra-low volume liquid ( vub), ultra low volume suspension
(vub), granules or tablets dispersible in water, water dispersible powder for treatment of sludges, granules or water-soluble tablets, water-soluble powder for seed treatment and wettable powder. These compositions include not only compositions ready to be applied to the plant or seed to be treated by a suitable device such as a spraying or dusting device, but also concentrated commercial compositions that must be diluted before they are applied to the culture. The fungicidal compositions of the present invention can be used to curatively or preventively control crop phytopathogenic fungi. A) Yes, according to a further aspect of the present invention, there is provided a method for preventively or curatively controlling crop phytopathogenic fungi characterized in that a fungicidal composition as defined above, is applied to the seed, the plant and / or the fruit of the plant or the soil in which the plant is growing or in which it is desired to grow. The composition such as that used against phytopathogenic fungi of crops comprises an effective and non-phytotoxic amount of an active material of general formula (I).
The term "effective and non-phytotoxic amount" refers to an amount of composition according to the invention that is sufficient to control or destroy the fungi present or likely to appear in the cultures and which does not imply any appreciable phytotoxicity symptom for said crops. Such an amount may vary within a wide range depending on the fungi to be controlled or controlled, the type of crop, the climatic conditions and the compounds included in the fungicidal composition according to the invention. This amount can be determined by systematic field tests, which are within the capabilities of a person skilled in the art. The method of treatment according to the present invention is useful for treating propagation material such as tubers or rhizomes, but also seeds, seedlings or transplanted seedlings and plants or plants that are transplanted. This method of treatment can also be useful for treating roots. The treatment method according to the present invention may also be useful for treating the aerial parts of the plant such as: trunks, stems or stems, leaves, flowers and fruits of the plant in question. Among the plants that can be protected by the method according to the invention, there may be mentioned: cotton; linen; vine; fruit crops such as Rosaceae sp. (for example, fruits with seeds such as apples and pears, but also stone fruits such as apricots, almonds and peaches), Ribesioidae sp. , Juglandaceae sp. , Betulaceae sp. , Anacardiaceae sp. , Fagaceae sp. , Moraceae sp. , Oleaceae sp_. , Actinidaceae sp. , Lauraceae sp. , Musaceae sp. (for example, bananas and plantains), Rubiaceae sp. , Theaceae sp. , Sterculiceae sp. , Rutaceae sp. (for example, lemons, oranges and grapefruit), - legume crops such as Solanaceae sp. (for example, tomatoes), Liliaceae sp. , Asteraceae sp. (for example, lettuce), Umbelliferae sp. , Cruciferae sp. , Chenopodiaceae sp. , Cucurbi taceae sp. , Papilionaceae sp. (for example, peas), Rosaceae sp. (for example, strawberries); large crops such as Graminae sp. (for example, corn, cereals such as wheat, rice, barley and triticale), Asteraceae sp. (for example, sunflower), Cruciferae sp. (for example, rapeseed), Papilionaceae sp. (for example, soybean), Solanaceae sp. (for example, potatoes), Chenopodiaceae sp. (for example, beet); horticultural and arboreal crops; as well as the genetically modified homologs of these crops. Among the plants and the possible diseases of these plants protected by the method according to the present invention, there must be mentioned: - wheat, as regards the fight against the following diseases of the seeds: fusariosis (Microdochium nivale and Fusarium roseum), coal covered with wheat (Tilletia caries, Tilletia controversa or Tilletia indica), septoria (Septoria nodorum) and naked charcoal; - Wheat, as regards the control of the following diseases of the aerial parts of the plant: ocular spot of the cereal (Tapesia -_ yallundae, Tapesia acuiformis), foot disease (Gaeumannomyces graminis), foot blight (F culmorum, F. graminearum), black spots (Rhizoctonia cerealis), powdery mildew (Erysiphe graminis form specie tri tici), rusts (Puccinia striiformis and Puccinia recóndi ta) and septoriosis (Septoria tri tici and Septoria nodorum); - wheat and barley, as regards the fight against bacterial and viral diseases, for example yellow mosaic of barley; - barley, as regards the control of the following seed diseases: reticular spots
(Pyrenophora graminea, Pyrenophora teres and Cochliobolus sativus), naked charcoal (Ustilago nuda) and fusaria (Microdochium nivale and Fusarium roseum); - barley, as regards the fight against the following diseases of the aerial parts of the plant: ocular spot of the cereal (Tapesia yallundae), reticular spots (Pyrenophora teres and Cochliobolus sativus), powdery mildew (Erysiphe graminis forma specie hordei) , dwarf rust (Puccinia hordei) and scald of barley (Rhynchosporium secalis); - potato, as regards the control of diseases of the tubers (in particular Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Fusarium solani), downy mildew (Phytopthora infestans) and certain viruses (Y virus); - potato, as regards the fight against the following diseases of the leaves: early blight
~ (Al ternaría solani), mildew (Phytophthora infestans); - cotton, as regards the control of the following diseases of young plants obtained from seeds: fall of mastic and basal rot (Rhizoctonia solani, Fusarium oxysporum) and black rot of the root (Thielaviopsis basicola); protein-producing crops, for example peas, in the fight against the following seed diseases: anthracnose (Ascochyta pisi, Mycosphaerella pinodes), fusariosis (Fusarium oxysporum), gray mold (Botrytis cinerea) and mildew (Peronospora) pisi); - oil-producing crops, for example, rapeseed, with respect to the control of the following seed diseases: Phoma lingam, Al ternarla brassicae and Sclerotinia sclerotiorum; - maize, as regards the control of seed diseases: (Rhizopus sp., Penicillium sp.,
'Trichoderma sp. , Aspergillus sp. , and Gibberella fujikuroi); - flax, in what refers to the fight against the diseases of the seeds: When ternarla linicola; - forest trees, as regards the fight against falling mastic (Fusarium oxysporum, Rhizoctonia solani); - rice, in terms of combating the following diseases of the aerial parts: parasitic Bruzzone (Magnaporthe grisea), spots on the edges of the pods (Rhizoctonia solani); legume crops, in terms of combating the following diseases of the seeds or outbreaks that emerge from the seeds: fall of mastic and basal rot (Fusarium oxysporum, Fusarium roseum, Rhizoctonia solani, Pythium sp.); - leguminous crops, as regards the control of the following diseases of the aerial parts: gray mold (Botrytis sp.), powdery mildew (in particular Erysiphe cichoracearum, Sphaerotheca fuliginea and Leveillula taurica), fusarium (Fusarium oxysporum, Fusarium roseum ), leaf spots (Cladosporium sp.), alternating (Al ternaria sp.), anthracnose (Colletotrichum sp.), septoria (Septoria sp.), black spots (Rhizoctonia solani), mildius (for example, Bremia lactucae, Peronospora) sp.,
Pseudoperonospora sp. , Phytophthora sp. ); - fruit trees, in regard to diseases of the aerial parts: diseases by monilia (Monilia fructigenae, M. laxa), scab (Venturia inaequalis), powdery mildew (Podosphaera leucotricha); - vine, as regards diseases of the leaves: in particular gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), black scab (Guignardia biwelli) and mildew (Plasmopara, viticulture); beet, in terms of combating the following diseases of the aerial parts: blight (Cercospora beticola), powdery mildew (Erysiphe beticola), leaf spots (Ramularia beticola). The fungicidal composition according to the present invention can also be used against fungal diseases capable of growing on or within the wood. The term "wood" refers to all types of wood species and to all types of wood work intended for construction, for example, solid wood, high density wood, laminated wood and plywood. The method for treating the wood according to the invention comprises essentially contacting one or more compounds of the present invention or a composition according to the invention; this includes, for example, direct application, spraying, immersion, injection or any other suitable means. The fungicidal composition according to the present invention can also be used in the treatment of organisms genetically modified with the compounds according to the invention or the agrochemical compositions according to the invention. Genetically modified plants are plants in which a genome has been stably integrated into a heterologous gene that encodes a protein. The expression "heterologous gene encoding a protein of interest" essentially means genes that bring to the transformed plant new agronomic properties or genes to improve the agronomic quality of the transformed plant. The dose of active material normally applied in the treatment according to the present invention is generally and advantageously between 10 and 2,000 g / ha, preferably between
and 1,500 g / ha for applications in leaf treatment.
The dose of active substance applied is generally and advantageously between 1 and 200 g per 100 kg of seeds, preferably between 2 and 150 g per 100 kg of seeds in the case of seed treatment. It is clearly understood that the doses indicated above are given as illustrative examples of the invention. A person skilled in the art will know how to adapt the application doses according to the nature of the crop to be treated.
The compositions according to the present invention can also be used for the preparation of composition useful for curative or preventive treatment of fungal diseases in humans and animals such as, for example, mycosis, dermatosis, trichophyton diseases and candidiasis or diseases caused by Aspergillus. spp. or Candida spp. , for example Aspergillus fumigatus or Candida albicans, respectively. The present invention will now be illustrated with the following examples: Example 1: Ficacy against Pyrenophora teres of a composition containing N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} - 2-trifluoromethylbenzamide (Compound 1) and trifloxystrobin The tested active ingredients were prepared by crucible homogenization in a mixture of acetone / tween / water. This suspension was then diluted with water to obtain the desired concentration of active material. The barley plants (variety Express), in seedbeds, seeded on a 50/50 substrate of peat-pozzolana and maintained at 122 ° C, were treated in the 1-leaf stage (10 cm) by spraying them with the aqueous suspension described above. The plants, used as controls, were treated with an aqueous solution that did not contain the active material. After 24 hours, the plants were contaminated by spraying with an aqueous suspension of Pyrenophora teres spores (12,000 spores per ml). The spores were collected from a 12-day culture. The contaminated barley plants were incubated for 24 hours at about 20 ° C and 100% relative humidity and then for 12 days at 80% relative humidity. The classification (% efficiency) was carried out 12 days after the contamination, in comparison with the control plants. The following table summarizes the results obtained when compound 1 and trifloxystrobin are tested alone and in a 1/1 weight ratio mixture.
According to the Coiby method, a synergistic effect of the mixtures tested has been observed. Example 2: Efficacy against AZternaria brassicae (in vitro) of a composition containing N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoramethylbenzamide (Compound 1) and trifloxystrobin The growth of Al ternaria brassicae was followed in PDA medium containing the compounds alone or as a mixture. The PDA medium was prepared by mixing 39 grams of PDA (Merck) in 1 liter of demineralized water. The medium was sterilized by autoclaving for 15 minutes at 121 ° C. The compounds were dissolved in acetone and added to the medium before pouring into Petri dishes. After drying the medium, the fungus was inoculated into the medium and allowed to grow at 19 ° C. The percentage of efficacy is indicated after 14 days of growth (measurement of radial growth) of the fungi compared to a control. what
According to the Coiby method, a synergistic effect of the mixtures tested has been observed. Example 3: Ficacy against Alternaria brassicae (in vitro) of a composition containing N-. { 2- [3-chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoromethylbenzamide (Compound 1) and azoxystrobin The growth of Al ternaria brassicae was followed in PDA medium containing the compounds alone or as a mixture. The PDA medium was prepared by mixing 39 grams of PDA (Merck) in 1 liter of demineralized water. The medium was sterilized by autoclaving for 15 minutes at 121 ° C. The compounds were dissolved in acetone and added to the medium before pouring into Petri dishes. After drying the medium, the fungus was inoculated into the medium and allowed to grow at 19 ° C. The percentage of efficacy is indicated after 14 days of growth (measurement of radial growth) of the fungi compared to a control. The following table summarizes the results obtained when testing compound 1 and azoxystrobin alone and in mixtures of different weight ratios.
According to the Coiby method, a synergistic effect of the mixtures tested has been observed. Example 4: Efficiency against Erysiphe graminis f. sp. tritici of a composition containing N-. { 2- [3-chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoramethylbenzamide (Compound 1) fluoxastrobin The active ingredients tested were prepared by homogenization in a crucible in a mixture of acetone / tween / water. This suspension was then diluted with water to obtain the desired concentration of active material. Wheat plants (variety Audace) in seedbeds, planted on 50/50 peat-pozzolan substrate and maintained at 12 ° C, were treated in the 1-leaf stage (10 cm stem) by spraying with the aqueous suspension described above .
The plants, used as controls, were treated with an aqueous solution that did not contain the active material. After 24 hours, the plants were contaminated by sprinkling them with spores of Erysiphe graminis f. sp. tri-tici, being dusted using contaminated plants. The classification was carried out 7 to 14 days after the contamination, comparing with the control plants. The following table summarizes the results obtained when compound 1 and fluoxastrobin are tested alone and in a mixture of weight ratio 8: 1.
According to the Coiby method, a synergistic effect of the mixture tested has been observed.
Example 5: Ficacy versus Botrytis cinérea de xana composition that contains N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} - 2-trifluoromethylbenzamide (Compound 1) and kresoxim-methyl The active ingredients tested were prepared by crucible homogenization in a mixture of acetone / tween / water. This suspension was then diluted with water to obtain the desired concentration of active material. Gherkin plants (Petit vert de Paris variety) in seedbeds, seeded on a 50/50 substrate of turpentine and maintained at 18-20 ° C, were treated at the Zll cotyledon stage by spraying with the aqueous suspension described above. The plants, used as controls, were treated with an aqueous solution that did not contain the active material. After 24 hours, the plants were contaminated by depositing drops of an aqueous spore suspension of Botrytis cinerea (150,000 spores per ml) on the upper surface of the leaves. The spores were collected from a 15-day culture and suspended in a nutrient solution composed of: - 20 g / l of gelatin - 50 g / l of cane sugar - 2 g / l of NH4N03 - 1 g / l of KH2P04 The contaminated gherkin plants were kept for 5/7 days in a climatic chamber at 15-11 ° C (day / night) and at a relative humidity of 80%. The classification was carried out 5 to 7 'days after the contamination, in comparison with the control plants. The following table summarizes the results obtained when compound 1 and kresoxim-methyl are tested alone and in mixtures of different ratios by weight.
According to the Coiby method, a synergistic effect has been observed in the mixtures tested. Example 6: Ficacy against Botrytis cinerea of a composition containing N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoromethylbenzamide (Compound 1) and picoxystrobin The tested active ingredients were prepared by crucible homogenization in a mixture of acetone / tween / water. This suspension was then diluted with water to obtain the desired concentration of active material.
Gherkin plants (Petit vert de Paris variety) in seedbeds, seeded on a 50/50 peat-pozzolan substrate and maintained at 18-20 ° C, were treated at the cotyledon Zll stage by spraying with the aqueous suspension described above. The plants, used as controls, were treated with an aqueous solution that did not contain the active material.
After 24 hours, the plants were contaminated by depositing drops of an aqueous suspension of spores of Botrytis cinerea (150,000 spores per ml) on the upper surface of the leaves. The spores were collected from a 15-day culture and suspended in a nutrient solution composed of: - 20 g / l of gelatin - 50 g / l of cane sugar - 2 g / l of NH4N03 - 1 g / l of KH2P04 Contaminated gherkin plants were deposited for 5/7 days in a climatic chamber at 15-11 ° C (day / night) and 80% relative humidity. The classification was carried out 5 to 7 days after the contamination, compared to the control plants. The following table summarizes the results obtained when compound 1 and picoxystrobin are tested alone and in mixtures of different weight ratios.
According to the Coiby method, a synergistic effect has been observed in the mixtures tested. Example 7: Ficacy versus Botrytis cinerea of a composition containing N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoromethylbenzamide (Compound 1) and pxraclostrobin The tested active ingredients were prepared by crucible homogenization in a mixture of acetone / tween / water. This suspension was then diluted with water to obtain the desired concentration of active material. Gherkin plants (Petit vert de Paris variety) in seedbeds, seeded on a 50/50 substrate of peat-pozzolana and maintained at 18-20 ° C, were treated in the Zll cotyledon stage by spraying with the aqueous suspension described above. The plants, used as controls, were treated with an aqueous solution that did not contain the active material.
After 24 hours, the plants were contaminated by depositing droplets of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on the upper surface of the leaves. The spores were collected from a 15-day culture and suspended in a nutrient solution composed of: - 20 g / l of gelatin - 50 g / l of cane sugar - 2 g / l of NH4N03 - 1 g / l of KH2P04 Contaminated gherkin plants were deposited for 5/7 days in a climatic chamber at 15-11 ° C (day / night) and 80% relative humidity. The classification was carried out 5 to 7 days after the contamination, in comparison with the control plants. The following table summarizes the results obtained when compound 1 and pyraclostrobin are tested alone and in mixtures of different ratios by weight.
According to the Coiby method, a synergistic effect has been observed in the mixtures tested. Example 8: Efficacy against Botrytis cinerea of a composition containing N-. { 2- [3-chloro-5- (trifluoromethyl) -2-pirxdinyl] ethyl} -2-trifluoromethylbenzamide (Compound 1) and 2-. { 2- [6- (3-Chloro-2-methylphenoxy) -5-fluoro-pyrimidin-4-yloxy] -phenyl} 2-methoxyimino-N-methoxylacetamide (Compound A) The tested active ingredients were prepared by crucible homogenization in a mixture of acetone / tween / water. This suspension was then diluted with water to obtain the desired concentration of active material. Gherkin plants (Petit vert de Paris variety) in seedbeds, seeded on a 50/50 substrate of peat-pozzolana and maintained at 18-20 ° C, were treated in the Zll cotyledon stage by spraying with the aqueous suspension described above. The plants, used as controls, were treated with an aqueous solution that did not contain the active material.
After 24 hours, the plants were contaminated by depositing drops of an aqueous spore suspension of Botrytis cinerea (150,000 spores per ml) on the upper surface of the leaves. The spores were collected from a 15-day culture and suspended in a nutrient solution composed of: - 20 g / l of gelatin - 50 g / l of cane sugar - 2 g / l of NH4N03 - 1 g / l of KH2P04 Contaminated gherkin plants were deposited for 5/7 days in a climatic chamber at 15-11 ° C (day / night) and 80% relative humidity. The classification was carried out 5 to 7 days after the contamination, in comparison with the control plants. The following table summarizes the results obtained when testing compound 1 and compound A alone and in mixtures of different weight ratios.
According to the Coiby method, a synergistic effect of the tested mixtures has been observed. Example 9: Ficacy versus Erysiphe graminis f. sp. tritici of a composition containing N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoromethylbenzamide (Compound 1) and dimoxystrobin The formulated compounds were diluted with water to obtain the desired concentration of active material. Wheat plants (Audace variety) in seedbeds, sown on 50/50 peat-pozzolana substrate and maintained at
12 ° C, were treated in the 1 leaf stage (10 cm stem) by spraying with the aqueous suspension described above. The plants, used as controls, were treated with an aqueous solution that did not contain the active material. After 24 hours, the plants were contaminated by sprinkling them with spores of Erysiphe graminis f. sp. tritici, dusted using contaminated plants. The classification was carried out 7 to 14 days after the contamination, comparing with the control plants. The following table summarizes the results obtained when compound 1 and dimoxystrobin are tested alone and in a mixture in a weight ratio of 1/8.
According to the Coiby method, a synergistic effect has been observed in the mixture tested. Example 10: Efficacy against Botrytis cinerea of a composition containing N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoromethylbenzamide (Compound 1) and N- [2- (1, 3-dimethyl-butyl) -phenyl] -5-fluoro-l, 3-dimethyl-lH-pyrazole-4-carboxamide (Compound B) The ingredients Assayed active ingredients were prepared by crucible homogenization in a mixture of acetone / tween / water. This suspension was then diluted with water to obtain the desired concentration of active material. Gherkin plants (Petit vert de Paris variety) in seedbeds, seeded on a 50/50 substrate of peat-pozzolan and maintained at 18-20 ° C, were treated in the Zll cotyledon stage by spraying with the aqueous suspension described above. The plants, used as controls, were treated with an aqueous solution that did not contain the active material.
After 24 hours, the plants were contaminated by depositing drops of an aqueous spore suspension of Botrytis cinerea (150,000 spores per ml) on the upper surface of the leaves. The spores were collected from a 15-day culture and suspended in a nutrient solution composed of: - 20 g / l of gelatin - 50 g / l of cane sugar - 2 g / l of NH4N03 - 1 g / l of KH2P04 Contaminated gherkin plants were deposited for 5/7 days in a climatic chamber at 15-11 ° C (day / night) and 80% relative humidity. The classification was carried out 5 to 7 days after the contamination, in comparison with the control plants. The following table summarizes the results obtained when testing compound 1 and compound B alone and in a 9/1 weight ratio mixture.
According to the Coiby method, a synergistic effect has been observed in the mixture tested. ? example 11:? fxcacia in front of Sphaerotheca fuliginea of a composition containing N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoramethylbenzamide (Compound 1) and boscalid The tested active ingredients were prepared by crucible homogenization in a mixture of acetone / tween / water. This suspension was then diluted with water to obtain the desired concentration of active material. Gherkin plants (variety Vert petit de Paris) in seedbeds, planted on a 50/50 peat-pozzolan substrate and maintained at 20 ° C / 23 ° C, were treated in the 2-leaf stage by spraying with the aqueous suspension described previously. The plants, used as controls, were treated with an aqueous solution that did not contain the active material. After 24 hours, the plants were contaminated by spraying with an aqueous spore suspension of Sphaerotheca fuliginea (100,000 spores per ml). The spores were collected from a contaminated plant.The contaminated gherkins plants were incubated at approximately 20 ° C / 25 ° C and relative humidity of 60/70% .The classification (% efficiency) was carried out 21 days after of contamination, compared to control plants The following table summarizes the results obtained when compound 1 and boscalid are tested alone and in a mixture in a 1/1 weight ratio.
According to the Coiby method, a synergistic effect has been observed in the mixtures tested. Example 12: Efficacy against Sphaerotheca fuliginea of a composition containing N-. { 2- [3-chloro-5- (trifluorosmethyl) -2-pyridinyl] ethyl} -2-trifluoromethylbenzamide (Compound 1) and N- (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide (Compound C) The tested active ingredients were prepared by crucible homogenization in a mixture of acetone / tween / water. This suspension was then diluted with water to obtain the desired concentration of active material. Gherkin plants (variety Vert petit de Paris) in seedbeds, seeded on a 50/50 peat-pozzolana substrate and maintained at 20 ° C / 23 ° C, were treated in the 2-leaf stage by spraying with the aqueous suspension described previously. The plants, used as controls, were treated with an aqueous solution that did not contain the active material. After 24 hours, the plants were contaminated by spraying with an aqueous spore suspension of Sphaerotheca fuliginea (100,000 spores per ml). The spores were collected from a contaminated plant. The contaminated gherkin plants were incubated at approximately 20 ° C / 25 ° C and at a relative humidity of 60/70%. The classification (% efficiency) was carried out 21 days after the contamination, in comparison with the control plants. The following table summarizes the results obtained when testing compound 1 and compound C alone and in mixtures of different weight ratios.
According to the Coiby method, a synergistic effect has been observed in the mixtures tested. Example 13: Efficacy against Alternaria brassicae of a composition containing N-. { 2- [3-chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoromethylbenzamide (Compound 1) and fenamidone The formulated compounds were diluted with water to obtain the desired concentration of active material. The radish plants (Pernot variety), in seedbeds, planted on a 50/50 peat-pozzolan substrate and maintained at 18-20aC, were treated in the cotyledon stage by spraying them with the aqueous suspension described above. The plants, used as controls, were treated with an aqueous solution that did not contain the active material. After 24 hours, the plants were contaminated by spraying them with an aqueous suspension of Al ternaria brassicae spores (40,000 spores per cm 3). The spores were collected from a 12-13 day culture. The contaminated radish plants were incubated for 6-7 days at about 18SC, in a humid atmosphere. The classification was carried out 6 to 7 days after the contamination, comparing with the control plants. The following table summarizes the results obtained when compound 1 and fenamidone are tested alone and in a 1/27 weight ratio mixture.
According to the Coiby method, a synergistic effect of the mixture tested has been observed. Example 14: Efficacy against Botrytis cinerea of a composition containing N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoromethylbenzamide (Compound 1) N- [2- (1,3-dimethylbutyl) -thiophen-3-yl] -1-methyl-3- (trifluoramethyl) -1H-pyrazole-4-carboxamide (Compound D) The compounds The formulations were diluted with water to obtain the desired concentration of active material.
The gherkin plants (Petit vert de Paris variety) in seedbeds, planted on a 50/50 peat moss substrate and maintained at 18-20 ° C, were treated in the Zll cotyledon stage by spraying with the aqueous suspension described above. . The plants, used as controls, were treated with an aqueous solution that did not contain the active material.
After 24 hours, the plants were contaminated by depositing drops of an aqueous spore suspension of Botrytis cinerea (150,000 spores per ml) on the upper surface of the leaves. The spores were collected from a 15-day culture and suspended in a nutrient solution composed of: - 20 g / l of gelatin - 50 g / l of cane sugar - 2 g / l of NH4N03 - 1 g / l of KH2P04 The contaminated gherkin plants were deposited for 5/7 days in a climatic chamber at 15-11 ° C (day / night) and 80% relative humidity. The classification was carried out 5 to 7 days after the contamination, in comparison with the control plants. The following table summarizes the results obtained when testing compound 1 and compound D alone and in mixtures of different ratios by weight.
According to the Coiby method, a synergistic effect has been observed in the mixtures tested. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.
Claims (20)
- CLAIMS? Having described the invention as above, claim as property is contained in the following claims: 1. A composition characterized porgue comprises: a) a pyridylethylbenzamide derivative of general formula where: - p is an integer equal to l, 2, 3 or 4; - q is an integer equal to 1, 2, 3, 4 or 5; - each substituent X is chosen, independently of the others, as being halogen, alkyl or haloalkyl; - each substituent Y is chosen, independently of the others, as being: halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, amino, phenoxy, alkylthio, dialkylamino, acyl, cyano, ester, hydroxy, aminoalkyl, benzyl, haloalkoxy, halosulfonyl, halothioalkyl, alkoxyalkenyl, alkylsulfonamide, nitro, alkylsulfonyl, phenylsulfonyl or benzylsulfonyl; as to the 2-pyridine N-oxides thereof; and b) a compound capable of inhibiting electron transport of the respiratory chain in phytopathogenic fungal organisms; in a weight ratio of (a) / (b) from 0.01 to 20.
- 2. A composition according to claim 1, characterized in that p is 2.
- 3. A composition according to claim 1 or 2, characterized in that q is 1 or 2.
- 4. A composition according to any of claims 1 to 3, characterized in that X is chosen, independently of the others, as being halogen or haloalkyl.
- 5. A composition according to any of claims 1 to 4, characterized in that X is independently selected from the others, such as being a chlorine atom or a trifluoromethyl group.
- 6. A composition according to any of claims 1 to 5, characterized in that Y is chosen, independently of the others, as being halogen or haloalkyl.
- A composition according to any of claims 1 to 6, characterized in that Y is chosen, independently of the others, as being a chlorine atom or a trifluoromethyl group.
- 8. A composition according to any of claims 1 to 7, characterized in that the compound of general formula (I) is: - N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2- trifluoromethylbenzamide; - N- { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2- iodobenzamide or N-. { 2- [3,5-dichloro-2-pyridinyl] ethyl} -2-trifluoromethylbenzamide. .
- A composition according to claim 8, characterized in that the compound of general formula (I) is N-. { 2- [3-Chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2-trifluoromethylbenzamide.
- 10. A composition according to any of claims 1 to 9, characterized in that the compound capable of inhibiting electron transport of the respiratory chain in phytopathogenic fungal organisms is a compound capable of inhibiting reduced nicotinamide adenine dinucleotide dehydrogenase in phytopathogenic fungal organisms. .
- 11. A composition according to claim 10, characterized in that the compound capable of inhibiting the transport of electrons from the respiratory chain in phytopathogenic fungal organisms is diflumetorin.
- 12. A composition according to any of claims 1 to 9, characterized in that the compound capable of inhibiting electron transport of the respiratory chain in phytopathogenic fungal organisms is a compound capable of inhibiting succinate dehydrogenase in phytopathogenic fungal organisms.
- 13. A composition according to claim 12, characterized in that the compound capable of inhibiting electron transport of the respiratory chain of succinate dehydrogenase in fungal organisms -phitopathogenic is: N- [2- (1,3-dimethyl-butyl) -phenyl] -5-fluoro, 3-dimethyl-lH-pyrazole-4-carboxamide, N- (3 ',' -dichloro- 5- fluoro-biphenyl-2-yl) -3- (difluoromethyl) -l-methyl-1H-pyrazole-4-carboxamide, N- [2- (1,3-dimethylbutyl) -thiophen-3-yl] -1- methyl-3- (trifluoromethyl) -lH-pyrazole-4-carboxamide, benodanil, carboxin, fenfuram, flutolanil, furametpyr, mepronil, boscalid, oxycarboxine or tifluzamide.
- 14. A composition according to any of claims 1 to 9, characterized in that the compound capable of inhibiting the transport of electrons from the respiratory chain in phytopathogenic fungal organisms is a compound capable of inhibiting mitochondrial ubiquinol: ferricytochrome-c-oxidoreductase in phytopathogenic fungal organisms.
- 15. A composition in accordance with the claim 14, characterized in that the compound capable of inhibiting the transport of electrons from the respiratory chain of mitochondrial ubiquinol: ferricytochrome-c-oxidoreductase in phytopathogenic fungal organisms is a derivative of strobilurin, ciazofamid, fenamidone or famoxadone.
- 16. A composition according to claim 15, characterized in that the strobilurin derivative is: azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, methominostrobin, trifloxystrobin, pyraclostrobin, picoxystrobin or 2-. { 2- [6- (3-Chloro-2-methylphenoxy) -5-fluoro-pyrimidin-4-yloxy] -f-enyl} 2-methoxyimino-N-methylacetamide.
- 17. A composition according to any of claims 1 to 16, characterized in that it further comprises a fungicidal compound (c).
- 18. A composition according to claim 17, characterized in that the compound (c) fungicide is selected from: captan, folpet, dodine, propineb, mancozeb, thiram, tolylfluanid, iminoctadine, dithianon, copper hydroxide, copper octanoate, oxycuroide of copper, copper sulfate, fosetil-Al, phosphorous acid, cymoxanil, iprovalicarb, benthiavalicarb, chlorothalonil, propamocarb, protioconazole, tebuconazole and spiroxamine.
- 19. A composition according to any of claims 1 to 18, characterized in that it also comprises a support, carrier, filler and / or surfactant acceptable from the agricultural point of view.
- 20. A method for preventative or curative control of crop phytopathogenic fungi, characterized in that an effective and non-phytotoxic amount of a composition according to any of claims 1 to 19 is applied to the seedling plant and / or the fruit of the plant or the soil in which it is grown or in which it is desired to grow the plant.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04356019 | 2004-02-12 | ||
EP04356096.0 | 2004-06-11 | ||
US60/637,120 | 2004-12-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
MXPA06009070A true MXPA06009070A (en) | 2007-04-10 |
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